Client Success Specialist

Northampton, MA

We’re looking for a dynamic, customer-focused professional to help onboard and support clients using our Payroll, HR, and Attendance platform! This hybrid-eligible role offers competitive pay and benefits, generous PTO, a modern and comfortable workspace, and plenty of team events.

Checkwriters is a payroll and HR services company focused on elevating every step of the customer experience. From interactions with our team to genuinely useful Payroll and HR software — we don’t just provide an excellent product. We have a team of experts who care about the details and work continuously to ensure that we provide our customers with the best experience they’ve had with a payroll and HR provider. 

Who we're looking for:

A motivated, relationship-driven individual with a passionate about helping businesses thrive. You bring honesty, reliability, and positivity to every interaction and you thrive in a fast-paced, client-facing role.

What you’ll do:

  • Guide new and existing clients through onboarding, upgrades, and product adoption
  • Coordinate onboarding timelines, communications, and project milestones
  • Build strong, trust-based relationships with clients and internal teams
  • Collaborate across departments to ensure a smooth post-onboarding handoff
  • Communicate progress updates and anticipate potential roadblocks
  • Identify opportunities to improve processes and enhance our products
  • Support special projects as needed

What you bring:

  • Experience delivering exceptional client-facing service (banking, HR, payroll, or insurance a plus)
  • Knowledge of HRIS, Payroll, or Attendance systems
  • Strong presentation skills and comfort learning software
  • Ability to understand client needs and keep projects moving
  • Flexibility, organization, and attention to detail
  • Proficiency with Microsoft Office
  • A team-first mindset, strong work ethic, and positive attitude

Candidates with experience in Banking, Finance, Human Resources, or Sales are encouraged to apply!